(2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: (2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 178271-94-8
• Molecular Formula: C₅₃H₅₈N₂O₁₁
• Molecular Weight: 899.05

Synonyms:(2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Chemical Property of (2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Chemical Property:

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Technology Process of (2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

There total 4 articles about (2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ethyl (2S,3R)-3-hydroxy-2-tert-butylcarbonylaminobutanoate (84500-44-7) → (2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (178271-94-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 4A molecular sieves, TfOH / CH₂Cl₂ / 1 h / -15 °C

2: TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

3: Et₃N, HPBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) 0 deg C to RT, 15 h

With trifluorormethanesulfonic acid; 4 A molecular sieve; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja952265x

Reference yield:

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite (153659-02-0) → (2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (178271-94-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 4A molecular sieves, TfOH / CH₂Cl₂ / 1 h / -15 °C

2: TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

3: Et₃N, HPBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) 0 deg C to RT, 15 h

With trifluorormethanesulfonic acid; 4 A molecular sieve; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja952265x

Reference yield:

Boc-(αFuc3,4,5Bn3)-L-Thr-OEt (174713-19-0) → (2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (178271-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

2: Et₃N, HPBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) 0 deg C to RT, 15 h

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja952265x

upstream raw materials:

N-Fmoc-trans-4-Hydroxy-L-Proline

(2S,3R)-2-Amino-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester

ethyl (2S,3R)-3-hydroxy-2-tert-butylcarbonylaminobutanoate

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite

Downstream raw materials:

5-{(2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

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